Today marks the 20th Anniversary of when my parents decided to immigrate to the United States of America.

I was 9.89 at the time. My brother was 7.

My Mom and Dad were in their early 40s and they embarked on a journey of not only reinventing their own lives, but their entire livelihood and the trajectory of how my little brother and I would grow up.

Today as I reflect on the past 20 years here, I can’t help but be thankful for all the benefits, advantages and opportunities that this great country has provided for me. My parents changed every aspect of their lives so I could live in a city like New York, so I could go to an amazing public school like Townsend Harris and an institution like RPI, and most importantly, they brought me to a place close to Silicon Valley where I could push my passion for technology well beyond my wildest dreams.

As a country, we face a tremendous number of challenges in these changing times. Same sex marriage, women’s rights, gun control and even immigration reform the agenda is endless. However, let’s not forget that it is far better to live on a land where such open dialogue and debate is happening vs a place where nothing is.

Say you want to start your own company. Or perhaps make a career change. Maybe you want to approach your boss about that that manager position thats open in your department.

These days, there are countless resources available at your disposal to help you think through this process and take the leap. There are user groups and weekend events entirely dedicated to jumpstarting your entrepreneurial career, tons of career coaches, and countless books and classes on the subject. Conferences are particularly great to get the right vibe going and get riled up to take that leap.

However, most people don’t.

Most people don’t leave that shitty job.

Most people don’t pursue that idea in a real way.

Most people don’t step up.

Most people just don’t show up.

Interestingly enough, no-shows are not only rampant in career related events, its also widely rampant in personal endeavors as well.

Here’s a picture of my Mom and Dad at roughly the same age Mahrin and I are now. Here’s a picture of us for comparison. What’s the difference? At that age, my Mom and Dad not only already had me, they were already thinking about having my brother. They showed up.

My Dad was running a successful business in Bangladesh, my Mom was playing full time Mom and part time school teacher, and they both were just making it happen.

The interesting thing here is, they had less.

My Dad had 10x less resources around starting a business back then in a country where entrepreneurship is still not encouraged. They both had 30x less resources around how to raise a kid and grow a family back then.

This is where Rule #1 comes in and truly exemplifies itself. There is never a perfect storm and perfect time to take that next step. There will only be troughs and peaks of imperfection and its up to us to capitalize on that and just step up, and show up. It is a universal truth that for things that we find daunting and hard, there has been countless people that has done it before us with less.

I think in today’s fast paced information packed society, when we do think about taking the next leap we get so inundated with the pitfalls and watch outs and the ins and outs, we forget Rule #1: Show Up.

Don’t wait for only that perfect moment. Start by just showing up.

Just show up.

“You can do that?” I thought.

Quickly I realized, why of course. Why couldn’t you lay comfortably and wait instead of doing what most of us were doing –  sitting in some awkward uneasy position awaiting instructions.

Unfortunately, unless you’re constantly ON and constantly thinking critically, most of our decisions and designs are geared to mimic what “most others” are doing. Rarely do we stop and say well, “How should this work?” or “What do I want?” or surely there’s a better way unless its something absolutely core.

Some think about how to be different for the big glaring things. Most don’t ever try to think differently for the smaller things.

However, companies and individuals that think critically about the smallest of things are the ones that truly innovate and make a huge impact.

Be a contrarian, not on the big things, but on the small things. Not for the sake for being a contrarian, but for the sake of finding a better way.

2010

By the end of 2010, I had already quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?.

As 2010 came to an end, Tout the most promising of the ideas I had been working on had acquired nearly a thousand users and even started generating revenues from day 2 of launching. Seems tiny in retrospect but for back then it was amazing. All I really had was a glimmer of an idea and a bit of market validation.

At that time, it was still just me. I was the Founder, Engineer, Designer, Marketer and Customer Support. But, beyond just me, others took a look and could tell there was something there. It was quite a bit of a contrarian view at the time. Instead of betting against email and trying to make everything “social”, even then, Tout was about making Email work better and believing that Email/Digital 1-to-1 communications would grow in usage and the tools we use to communicate would need to evolve.

2011

In 2011, I decided to drop everything else and concentrate all of my efforts on building Tout as a real company.

With the rise of convertible notes, accelerator programs and the general fundraising climate of 2011, I decided to switch from a bootstrapped startup and raise money for Tout.

Through 2011, I joined the 500 Startups Accelerator Program, built out a team of some seriously amazing people, Raised a seed round of nearly $800k from the likes of Esther Dyson, Eric Ries, Dave McClure and others, and built out ToutApp to what I like to call “Version 1.0″

Although I had made it a tradition to write a “Year In Review” post since 2009 or so, I ended up not writing one at the end of 2011. I had done so much, Tout had grown so much, and yet I felt no sense of finality as December rolled around.

2011 was Tout’s Foundational Year

Through the course of 2011, we grew our user base, we grew the footprint of our product, we grew our revenues. We talked to customers and got a core understanding of the problems we were solving. Looking back, it was a foundational year that every startup with a long enough view needs to have and needs to go through. However, as the end of 2011 rolled around, things didn’t feel all that great.

After spending the summer in California, it became evident that I needed to stay there instead of going back to New York to maximize the outcomes around the business. However, with a distributed team stemming from New York, Indiana and California, merging everyone into one place would be downright impossible.

Tout was my baby. Moving to California felt like a no-brainer to me. Fortunately, my wife was incredibly supportive as well and didn’t give moving a second thought either. However, it wasn’t the same case for the rest of the team. They weren’t founders. They had families, friends, lives that they couldn’t necessarily uproot. And so, Tout came back to being just me.

As the end of 2011 rolled around, we did a holiday promotion called “Your 2011 Email Year In Review.” Through the course of the holidays, we signed on 20,000 users, and got featured on The New York Times, Mashable, TechCrunch, and countless other publications. The servers crashed and burned, but somehow we got through it. We acquired users, converted to revenue and got our name out there.

No one knew it was all being done by a now-1-person company. Not even the New York Times.

It was a serious conundrum that even I couldn’t believe. As our transition to San Francisco brought down our actual team count to 1, our user base continued to grow. Our revenues continued to grow. And since I was already used to being the one-man-show, the product continued to get better.

2012 – Tout Grows Up

So as 2011 ended, I stayed calm and carried on; however, I couldn’t find the mindset to write down a “Reflecting on 2011″ blog post because of the utter lack of finality or at least one worth writing about.

As 2012 started, it became clearer than ever that Tout was onto something important. Even if my faith or my beliefs faltered for as second, our amazing customers and community constantly reminded us how Tout made a serious impact on their day to day which they would more than happily pay $30/month for. And so while in retrospect January was probably an insane month for me, at the time I felt like a surgeon standing in front of a dying patient with steady hands and a plan on what needed to be done.

As January rolled into February and onward through Q1 of 2012, we closed the remainder of our seed round with Founder Collective and a few others. What we needed to build for Tout to take the business to the next level was clear, and so I continued to set out to establish ourselves in San Francisco and make key hires in Support, Engineering, Sales and Marketing as we continued to grow our paid customer base.

As I look back at 2012, I can wholeheartedly say that its been the most intense, most stressful, most amazing, most balanced year of my life that I have ever lived. In other words, it has been the quintessential definition of an Entrepreneurs life at its extreme.

2012′s Focus Was on Product

Through the course of 2012, we’ve achieved what we call “full coverage” here at Tout meaning, we’re now fully and deeply integrated into Gmail, Outlook, Salesforce, iPhone, and all major web browsers. We’ve developed our on boarding, training, support, sales and marketing programs and we’ve figured out ways to predictively convert new customers to paying customers to retained customers in a systematic way.

We completely rebuilt Tout’s GUI from the ground up and expanded the platform well beyond simple Email Templates which is how Tout got its start back in 2010.

And most importantly, while I always referred to Tout as “we” even when it was just me, through 2012 we grew Tout’s team to make sure all key areas of our business including Engineering, Customer Happiness, Training, Marketing and Sales had smart individuals to think through a design and operate it like a well oiled and beautiful machine.

Don’t get me wrong. We’re still tiny, there’s only 6 of us. However, the ratios around the business and the amount we get done with just 6 people, never cease to astound me. As 2012 comes to an end, we have more computer screens than we have employees. We are integrated into more platforms than we have employees. While most SaaS companies enjoy < 1% of their user base as paying users, we have nearly 3% of our user base paying us for our B2B offering. And of course there’s my favorite, nearly 8% of users signing up every week will end up paying us with their credit card.

2012 – I Grew Up as a Startup CEO

While the end-state of 2012 feel a heck of a lot better than 2011, I’d be doing all of you a disservice if I wasn’t honest about exactly how hard, tiring and painful this year has been. There is absolutely nothing of certainty when you’re doing a startup. And for the better part of this year, I’ve slept very little at night because of that.

When you’re just starting out, like I was back in 2010 and through a good part of 2011, you have absolutely nothing. Having absolutely nothing is one of the best blessings one could ironically ask for. Having absolutely nothing means you’ve no reason to fear anything because you’ve got nothing to lose. The smart ones through this period go through a period of amazing wonderment trying different things, taking bigger and bigger risks, and doing anything and everything possible to make something to replace the nothing.

Once things start to click. Once that first big customers comes on. Once that really great investor comes on board. Once you win that really great deal it all changes. Its the dream of every startup founder, some call it product market fit, some warn of it as “be careful what you wish for.” Once you have something its a whole different game you start to play. Once you have something its no longer about doing anything and everything and seeing what sticks, it becomes a careful game of management.

Management is a term we think we understand, but until you really stop and think deeply about it, especially as a Startup CEO you don’t truly understand the breadth and weight of the responsibility.

2012 – On Not Sleeping At Night

As 2012 came to be and things started to progress with our product, our market, and our team, I entered into a mental state for the majority of this year that I believe has no real name or categorization but can only be attributed to serving in the role of Startup CEO.

The first thing that happens in this state is related to sleep. Sleep becomes redefined. It’s no longer “go to bed because you can call it a day” it’s more of a “well I guess now is the time to sleep but all you can do is lay awake and stare while your mind processes thinks and reevaluates scenarios at light speed.”

You start to incessantly check Twitter/LinkedIN/FB in the morning only to confirm that the darlings of Silicon Valley are still indeed killing it and you get another fire lit under you just so you can try and “catch up” today.

God forbid you do get featured profiled or become the darling now you work 10x harder than your already 100x pace because behind the scenes things still feel like you’re running an ugly dirty sausage factory.

Although you conceptually realize that this job is all about keeping your head in check you still struggle to deal with the raw emotions of it all.

2012, I Know Why We Work So Many Hours

The interesting thing is the emotions rarely come into play during office hours. Between the hours of 9 and 7 (on average) when I was actually in the office, it was like being in a symphony orchestra. You focus on the most important things, you code, you talk, you brainstorm, you fix problems, you DO things because then at least you feel like you’re doing something about the fear of failure you’re doing what you need to so you can carry things forward to the next level.

Maybe this is why we work so many hours. Not because we are so damn productive at our 80th hour of the week, its more because not working is just so damn unbearable.

Speaking of non-work-hours. At some point you probably signed up for a real life with real friends and real relationships. Through 2012, I had to either make a conscious decision to cut off those ties and make my company my life or decide to pursue that elusive “work-life” balance.

Fuck work life balance. You never actually achieve balance because you can’t stop thinking about it. But – you still go to the birthday parties, double dates, you drive your house guests to napa and you spend Sunday afternoons grocery shopping.

You talk you laugh but inevitable you get a little quiet. A little reserved. Truth is you’re just going through the motions. You’re not really there. You’re numb.

Inevitably they’ll ask how’s the company you put on your PR face and give the byte sized clips. Worst case – you say “great!” Even worse, they happen to mention the name of a competitor. Thats it. You can now clear out the rest of your night schedule at that point and sign yourself up for at least one more restless night.

2012, Mondays, Days, The Concept of a “Day”

And so when Monday rolls around you’re just exhausted from trying to be normal and escape numbness but now that Monday is here all you really want is a day alone where you can just hear yourself think. But that’s out the window because there’s a slew of customers, employees, investors etc roaring to go needing things doing things and so you just jump in.

Thats fine though, give it 10 minutes into the office, and then you’re back into the symphony orchestra again. It doesn’t matter how tired you are. You don’t even remember it anymore at this point. You’re in the zone. You love it.

At the end of your day your loving wife might ask you how your day went. She cares. She deeply cares and she wants to relate. Except to you it doesn’t feel like a “Day” it feels like you started your day last Thursday and haven’t skipped a beat and you’re already planning tomorrow and tinkling about next week and so your exhausted overworked mind literally has no synthesis on how TODAY went because for all practical purposes there is no today and no tomorrow there is just ON and OFF and you haven’t turned if OFF for god knows how long and you won’t till you reach your goal.

None of these things are good or bad. This is no ones fault except your own. Its my own fault. I signed up for this. Remember? I quit that 6 figure job so I could have this instead.

2012 – Goals

Goals. Thats a funny word in this stage of the company. We have milestones, weekly goals and you hit them or you were aggressive in goal setting and maybe you don’t. In the back of your mind though, you know very well that all of this is arbitrary. The only goal there really is the only one that really matters is when you’re “wildly successful.”

By now you’ll have forgotten how many times you pushed back that goal post. You won the little battles and you just kept pushing forward because every win felt like a small win and you felt like there was always something more and so you forged ahead because that’s the right thing to do and so at this point what is the goal really? Wild success. Killing it. IPO. Acquisition. Surviving.

2012 and My Partner In Crime

“Are you still enjoying this?” When my wife sees that I’m stressed out, she always asks me that. Its her way of reminding me where I’ve been, the decisions I’ve made, and reflecting on where I am. I love her for it. In fact, while I made it a policy to not let my wife work within Tout, I’m not exactly sure where I’d be if she wasn’t around. Through the course of 2012, she made sure I kept by Gout in check, she made sure I went to the gym 3 times a week even if it meant being the bad guy and nagging at me. She made sure breakfast and coffee was ready and a nutritious lunch and dinner was at arms reach. There has been two big empires I’ve been busy building through 2012, one is Tout and the other is our family with my wife. And to be honest, because of her and her support and her love, I have unparalleled faith in the success of both empires.

I’m Still Loving This

From a well paying desk job to nothing to something to now. Today, Tout stands strong as the most complete Sales Communications Platform. Through 2012, we’ve come together as a seriously amazing and fun team, we’ve brought on customers that are using our platform to do amazing things, and I can’t help but shed a tear when I watch this year-end video we put together featuring the state of Tout and the team.

2013

We’ve worked hard over the past 3 years and now we have a platform that is unparalleled. We’re switching from being inward and purely customer focused to expand into aggressive Sales and Marketing. This ain’t vaporware, this is a real throughly tested and deeply thought through solution now. We’re all seriously excited about making sure every Sales Team uses ToutApp.

Yes its hard. But this is Startup life.

Email me your thoughts: tk at toutapp dot com.

One of the biggest things I like to do is to look for patterns in life and draw them to core principles that weave together everything you do in your life. Core principes are powerful that way because no matter the situation, you can still apply them to solve problems.

My boxing instructor told me, if there is one thing I want you to learn in this class, its the “Jab, Punch Jab.” Meaning, if in the real world you ever have to defend yourself, you want to be able to deliver a powerful Jab, Punch and then a Jab and then get the fuck out of that situation.

For those of you that never really looked into boxing, a Jab is a quick pump of your left hand (for righties) that go right into the face. Its quick, fast, and you take a Jab with a quick step forward and then return to your position to re-asses the situation.

Once you jab, and you hit, you want to go for a full punch. A punch is a where you put in your whole body weight, let out a serious breath and use your right foot to “squash the bug” — lunge a bit forward and deliver a seriously strong blow to your opponent with your right hand.

And finally, while your opponent is literally flabbergasted with the Jab and the Punch, you want to finish the combination with another Jab. Except this time around, that same simple jab will have an even more profound blow building on the previous two blows you dealt to the opponent.

Thats the Jab, Punch, Jab.

I’ve found the same applies to Startups in terms of a core principle.

The most successful startup founders out there, in my opinion, start with a series of quick jabs to feel out different ideas. They take quick easy hits into problems they think they can solve. Some end up going into empty air, some end up being a partial hit, and then one ends up being a direct hit.

Most thriving startup founders today kept jabbing when they hit thin air, and as soon as they hit the bullseye on that first jab, capitalized on it and went for the punch — either through raising funding, starting the startup, expanding the product — but all in the sense of building on the jab and doing the harder work to solve the deeper problem.

And finally, they followed the punch with an even quicker jab – a jab that built on the punch, was just as effortless as the first jab, but had a seriously more profound effect because it built on the initial jab and the hard work of the punch.

So regardless of whether you’re looking to start a startup, in the midst of Heads Down Mode, or are just about to come out of a period where your team has been hard at work building some seriously defensible technology, remember the Jab, Punch, Jab principle.

If you’re just staring out, keep jabbing till you make a hit

If you just made that first jab and made a hit, figure out that seriously hard problem that needs to be solved and put in the hard work to go in for the punch. The punch takes time, takes effort, takes discipline, and is where most startups fail — but if you pull through then you deal a serious blow to your “opponent” and can follow up with a serious of jabs and combinations that have far deeper impact but are way more effortless for you than it would have been otherwise.

Once you’ve put in the hard work, look to finish out the combo with another Jab, a jab that builds on the hard work of the punch, a Jab that builds on what you’ve done so far, is just as effortless as the first, but would’ve been impossible to deliver without the punch, and delivers a profound impact.

Rinse, Repeat. Build. Win.

Jab, Punch, Jab.

Although this now pretty-standard graph outlines different stages that your company goes through, I don’t think it quite captures the stages that you yourself as the founder go through in your own head. As I reflected on the past year or so, I’ve been able to break down this period of heads down mode into two distinct mindsets: the bumbling period and the awareness period.

The Bumbling Period

One of the biggest points of discussion that stuck out in my mind about the heads down mode thread was that this is the period when tons of startups die. This is the period where if you’re not careful, resilient, and organized, you’ll basically lose sight of time, lose interest, or even worse, run out of money and fail to get to the promised land.

Obviously, when you’re deep in it, its hard to take a step back and realize where you are and what the pitfalls to watch out for are. The Lean Startup methodology teaches us build -> measure -> learn at all times, and to look at meaningful metrics at all times, but doesn’t speak much in terms of having the right mindset, outlook or basic organization around running and building a team/business.

In the earlier months of ToutApp once we raised funding, my first inclination was to push down hard on the gas pedal. We rented an apartment in Mountain View, and pretty much started working right after getting out of bed till late at night. This went on for 3 months. We had To-Do lists, we kept an eye on our metrics to make sure we were seeing incremental improvements, but there was just so much to do, all we knew was that we were behind and we needed to push as hard as possible in time for Demo Day so we can make things go “boom.”

The Awareness Period

Eventually you realize, this is not a sprint. Sure you can get lucky and strike gold and at the end of your sprint you can win Gold by tapping onto the perfect distribution channel and the perfect viral loop — but those things are 1) hard to come by 2) usually not a strong foundational thing (e.g. Turntable — which encountered this phenomenon during the same summer we started ToutApp).

Eventually, after you push through 3-months, after Demo Day, after even a couple more months, you realize that while there will be improvements to your metrics, it still takes quite a bit of time to build a solid and foundational business. A business. Not a consumer sensation, not a build it and flip it for an acqui-hire (which is finally getting the amount of hate it deserves), but a business, that makes money, maybe even a profit.

So eventually, you’ll come to realize this and you’ll either decide 1) you can’t do this, so you’ll stop and get a job again (nothing wrong with that) or 2) you’ll sit down, get comfortable and figure out how you’re going to manage things thing for the long run.

Welcome to the awareness period. This is when you know you’re going to be heads down and you’re going to have to work your ass off for a long period of time to make this baby fly.

Fear = Your Biggest Enemy

As you navigate from bumbling to awareness and forge ahead, I’ve come to realize that your biggest enemy over the coming months/years is going to be your own mind, your fear, and your own ability to visualize success. Secondarily, as a founder, its going to be your own ability to extend positive beliefs onto the rest of the team to keep them moving forward as well.

Now obviously experiencing fear is all natural. And probably expected. Each of us got in this game because at one point or other we were in a situation of stagnation and decided we wanted more. But fear is probably the key thing that can lead to the greatest detriment during heads down mode — atleast in my mind.

I found that as soon as I could get my fear into check everything else became 10x easier.

A Calendar and a Graph

Now, to be honest, it took me a few months to come to a point where I had my fear in check. I did it by trying a whole lot of different things right along with working as hard as possible. But through my experimentation, I found these two key things to be the biggest help in staying aware, staying calm and carrying on:

1. A 6-Month Calendar: In the main whiteboard at our office, we keep a whiteboard that maps out the next 6 months, with each month divided into 4 boxes. And in those boxes, we decided listed out as a team what our top 1-3 priorities for the week would be. These weren’t our tasks for the week, nor were they list of projects or anything. These were concerete things we wanted to work on and improve through the week. Not only did this help us “write the story” of what our next 6 months would be like, it gave us a good idea of whats important every week, where we’re headed and how things are going.We revisited this calendar every Monday morning and reviewed how the previous week went, whether we needed to reshift our priorities for this week or the coming weeks and how our overall plan was looking.

   Not only did this help us stay organized, it helped give me and the whole team piece of mind — it became our compass.

2. A Graph of our Atomic Unit: the atomic unit for our service is an email. Fred Wilson recently blogged about the importance of knowing what the atomic unit for your business is. While there are a lot of other metrics that we look at, I always kept an eye on this guy because it told me over time whether we were fundamentally getting better in terms of usage (the thing that matters the most for any business).

In Conclusion

As I mentioned in my last entry, I don’t claim to have all the answers. In fact, I still continue to experiment and explore. But so far, this has been working quite well for myself and our team. The biggest thing I want to do is to get more founders talking about this heads down mode. To share more experiences, to have an outlet, and to talk more about what works and what doesn’t.

There has been two distinct stages to my life so far: 1) The stage where I started ToutApp and become a Startup Founder and 2) The stage where I dreamt of starting my own from scratch and lived vicariously through other startup founder blogs, TechCrunch and the 37Signals blog.

The one thing I always promised myself I wouldn’t do was go into the abyss once I actually started my company. I hated it when Founders made a ton of noise, shared a ton of insights, get a ton of PR, passionately talk about their startups but then went into complete silent mode shortly after they raised funding or hit a couple of milestones.

Needless to say, I did the exact thing that I found myself hating on others for. As ToutApp grew over the past few months, and as I switched cities, raised funds, defined the vision for the company and grew the team, I blogged less and less. I shared less and less insights. Even though I moved to Silicon Valley from New York because of the connected eco-system here, I’ve gone to exactly 2 networking events and one of them was by accident.

Why Founders Go Silent

So in true form of how this blog works, I decided to reflect upon why I went into silent mode. The easy answer is that I was too busy and no longer prioritized sharing my learnings with others. But I don’t think thats actually true. I still continued to talk to other founders and share my insights whenever someone reached out to me; infact, it is something I really enjoyed.

The slightly less of a copout answer is that I just didn’t want to be as transparent as I once was. As ToutApp grew to understand its market, its customers and develop our product, copycats started to arise. Whoever said that “imitation is a form of flattery” was bullshitting, its not flattering at all, its simply annoying especially when ideas you have worked hard to think deeply about and develop are copied into cheap knockoffs.

To say that competition and my need for less transparency was the reason I didn’t share as much about what I’ve been doing still feels like a copout. Dealing with competition deserves a separate blog entry of its own but I truly believe that the best way to beat your competition is to check in on them once a month but by and large ignore them and shift that energy toward stalking your customers — and so with that spirit, saying that I don’t share more of my thoughts because the competition will get a view into my thinking process is also not a real answer.

So finally, with those two relatively easy answers being struck out, I was left with one cold hard truth: I was afraid to continue to blogging because I didn’t have any amazing mind-blowing news to report.

No Amazing Mind-Blowing News = You’re On Heads Down Mode

The biggest thing I’ve realized in the journey is really how long it takes to make your business a success. We’ve been at it with ToutApp for nearly two years now and while there has been a ton of tremendous and amazing milestones with more to come including us fast approaching a 1,000 paid seats, when you’re two years in, unless you are a rare exception, you’re still somewhere in-between the “trough of sorrow” and “the promised land” — otherwise known as “Heads Down Mode.”

And while there is a ton of learning happening as you’re navigating this treacherous territory, it just feels akward sharing any of your learnings because you just don’t know if its validated learning or just a misconception thats going to take you deeper into the “crash of ineptitude.”

And so, following a line of many other startup founders who I’ve hated on before, I ended up doing the same thing. As I buckled down, I went heads down into focusing on our team, our product, and our customers and thereby slowed down on PR, slowed down on blogging and most importantly slowed down on sharing my learning.

We need to talk more about being Heads Down Mode

Just to be clear, although I’ve justified why I haven’t been blogging, I think the reasons are fundamentally wrong.

I’m going to make a conscious effort to blog more actively about being in Heads Down mode and I think other startup founders need to make a conscious effort about talking about this as well. Yes things are tough, yes in one minute you’re thinking “Holy Shit, we’re going to be a billion dollar company” and in the next minute you’re thinking “What the hell did I do to my life?” And yes, you don’t quite know if the conclusions you’ve drawn and the decisions you’ve made will take you out to the promise land, but still share those thoughts and learnings so that we can all get better as a whole.

We’ve heard this story time and time again. Start starts, huge fan fare. Start blows up and becomes an overnight success, and huge fanfare again. No one ever talks about the 3 years that happened in-between where the real “entrepreneuring” happened.

Let’s change that.

Also, there is a great discussion thread going on over at Reddit.

Over the past week, I’ve been interviewing for the Lead Engineer position here at ToutApp. I’ve never been a fan of interviewing. No matter how elaborate the process, we all know it often comes down to that team huddle after the interview and gut-feeling comments like “I really liked her, she had a good vibe.”

I think hiring Engineers is even harder. I personally had to go through the Gnomes problem while at Plaxo and logic problems while interviewing for an internship at Goldman (wth was I thinking), and I hated every minute of it.

So, here at ToutApp, I take a more practical approach. When I interview engineers, I get in front of a white board and ask the person to build me a link-shortening service with an API.

Why a Link Shortener?

It started off as my go-to-example because we built one ourselves here at Tout and got to know the interesting intricacies of it. But the more I thought about it, the more I loved the idea of it because it covers many fundamental concepts behind systems design, service oriented architecture, proper database design and optimizations and even job queues and caching around a very simple and easy to understand use case.

Also, I never thought this would happen (but it did) — if a candidate had trouble grasping the concept around a link shortener, then he or she is definitely the wrong person for the job (instant filter).

Step 1 – Set the Context

The way this works best is to engage the candidate in a way so that he or she starts to draw out the overall architecture, database design, interactions and even certain parts of the code right on the whiteboard.

So, to get things started, I start off the diagram on the whiteboard listing out the key use cases I want my link shortening service to support.

1. I want a Link Shortener with an API that I can call from my web-app. I want to pass in a URL and I want the Link Shortener to give back a shortened URL that I can present to my user
2. When the shortened URL is visited by my users, I want the Link Shortener to redirect to the original URL
3. I want an API where I can query stats around a particular shortened URL giving me details about the users that have visited that URL with as much information as you can give me about each person

I want the candidate to be drawing the design, architecture and code on the whiteboard, so I always start off by drawing out a simple web-app box with two endpoints, one representing the request for a shortened URL and another representing the request for stats around a URL.

Step 2 – Start Drawing

At this point, you want to have the candidate pick up a marker and start talking through how he or she would go about designing the service. The key things you want him to write out are:

1. The routes your web-application should support
2. The models that you’d create for the web application and the database tables
3. The controllers (don’t get into pseudo code just yet)

1. I like to make sure they get detailed enough in terms of route names, url paths and model names. I’ve found that the way an engineer names objects and the conceptual model they create to organize their code base is a tremendous indicator of how good they are.
2. The other key thing I like to probe into is how they create their routes. Do they require a POST vs a GET when accepting a short URL request? Challenge their thinking around this, obviously you can go either way but the considerations they took to get to the decision will tell you how much they really know about the HTTP protocol and building a RESTful API.
3. Look out for the things you think are obvious. I had one candiate talk about how he would store the tracking data in the session and save on a database call (which made no sense). So even on the simple stuff, make sure you get them to explain how they’d handle the key aspects of the use cases.
4. Lastly, always link back to the three use cases you started by writing out. Those are three very loaded sentences — keep an eye to see if the candidate remembers to track the redirects, if he or she thinks about authenticating the API calls from your web service, and other things that aren’t obviously spelled out but an experienced hacker would know to think about.

Step 3 – Get into some Pseudo-Code

Although we’re primarily a Rails shop, we’ve interviewed people with backgrounds in Java and .NET as well. I figure that if they are truly strong programmers, they’ll be able to pick up Rails and Javascript fairly quickly. So at this point in the interview, I like to dig a little bit deeper into their coding abilities.

I ask them to write the pseudo-code for the controller action that addresses Use Case #2 – the redirect.

If  the candidate has trouble with Step 2, I always make sure I give them the benefit of doubt and help them along with the design to get them to this particular step. So at this point, assuming that he or she is not completely confused, they should be able to churn out some pseudo code like this:

def redirect
link = Links.find_by_short_url(params[:id])
visitor_information_from_header = parse_http_request_for_user_info(request)
LinkVisit.create(visitor_information_from_header)
redirect_to link.original_url
end

By this step, you’ll really be able to figure out a candidate thats pretty much full of shit and a candidate that understands the basics of programming. If you want, you can make the example more concrete and have them write real code (e.g. in Rails) so that you can test their understanding on how a framework like Rails encapsulates query strings, http headers, and how ActiveRecord works.

Step 4 – Test their knowledge on Architecture Patterns

At this point, I like to throw them a curve ball. I go up to the white board, and start to mark up the calls in their pseud-code with how rough estimates on how long each call would take. I try to use a red marker so that it stands out, and it looks something like this:

def redirect
link = Links.find_by_short_url(params[:id])  [60ms]
visitor_information_from_header = parse_http_request_for_user_info(request) [1ms]
LinkVisit.create(visitor_information_from_header) [60ms]
redirect_to link.original_url
end

I then say that user experience is of utmost importance to us, so we want to make sure that these redirect calls are done in under 20ms. I ask what he could do with this design so that we can accomplish that.

Your candidate should be able to talk through each of these core concepts (from easiest to hardest):

1. Create a database index on the short_url field in the Links table so that lookups are faster. [+10 points]
2. Make the short_url the clustered index and primary key for the Links table [+20 points]
3. Store links created in the past 30 days in an in-memory cache for easier lookup [+50 points]
4. Create a background job worker + queue that will take the vistor header information and will persist it to the database later [+100 points]

As you can see, even in a simple servie like a Link Shortener, there are a number of things you can do to drastically improve performance. Being able to talk through these simple patterns is what truly sets apart the boys from the men.

I also like to see if they suggest alternate ways of storing the data. Do they say we should use a document-based storage system instead of a Database? Do they want to use the shiny new technology just for the sake of using it and because they just learned a buzzword like NoSQL or can they back it up with sound thinking? This exercise is a great platform to have those kind of discussions and get at the root of his/her thinking process.

Step 5 – Test their knowledge on Software Patterns (optional)

Finally, if you’ve gotten this far, I delve a bit deeper into how he or she would organize the software code. What parts of it would be a standalone library and what parts of it would go straight into the controllers.

This is more to ramp down the conversation but the things I look for is whether they care enough to create a standalone library for hashing URLs, or whether they like to encapsulate the tracking code within the model or whether they prefer to do it all in the controller (and why).

Other things I like to talk about (and In Conclusion)

This exercise has proved to be way more effective than a lot of other styles I’ve employed while hiring in my career. It forces you to interact with each other, gives you a glimpse into their problem solving abilities, how he or she deals with pressure, how they deal with situations and concepts that are foreign and really puts the two of you “in the moment” as if you’re already on a team solving a problem.

In addition to this, I also like to talk through and gauge how much user empathy they have. These days, people that can cross between frontend, backend and design are the true rockstars and exactly what we’re looking for, so I like to get a feel for whether they “just like to code requirements” or they can truly get proactive and help us build product.

How do you interview engineers? Hate/Love this approach? Share your comments below or email me at tk@toutapp.com.

Shameless self-plug:

Want to join ToutApp as our first Lead Engineer? Apply here.

When I was young, I was really into Electronics. I loved taking my toys apart, stripping it down to the motor, lights and batteries and building something else with it. But, I was always limited by the extractable parts in my toys which inherently limited the actual things I could build with these parts. Most of the time, I ended up just making a fan out of the motor, the batteries, and some retrofitted wings.

This all changed when my Dad bought me this 60-in-1 from Radio Shack for my 10th birthday. It was perfect, it had a relay, capacitors, resistors, a AM antenna, a piezo buzzer and even switches to trigger different modes. It came with a guide book of 100+ projects that you could build based on the raw components that the project lab had. And best of all, as you worked through these projects, you learned how you can piece together these basic raw ingredients to create something totally unique.

Starter Kits

Ever since that 60-in-1, I have always been enamoured by the idea of “Starter Kits.” They are an amazing concept that can take any newbie or far standing admirer and figure out a way to spark raw passion in a step-by-step fashion.

Starter Kits aren’t easy to build though, because it takes  a ton of skill to take something essentially esoteric and strip it down to its raw necessary components so that a newbie can learn to engage with it. This is hard to do but the results are incredible and usually disruptive.

I believe that an entire businesses can be built (and has been built) from applying the idea of Starter Kits to different industries.

Why not have a Starter Kit of Entrepreneurs?

This got me thinking. Why not have a Starter Kit for Entrepreneurs? I think we already have the beginning stages of this: Accelerators and Incubators are all about giving the Entrepreneur the initial raw ingredients necessary to get started (and reach success).

I think the best kinds of Starter Kits are the ones that are productized. Accelerators/Incubators always have a financial relationship with Entrepreneurs which although is healthy with vested interest is not one of unlimited support (all the time).

What would be in this Starter Kit?

Here’s where it gets tricky. Interestingly enough, this Entrepreneur Starter Kit isn’t just a set of resistors and capacitors, this Starter Kit requires so much more beyond just inanimate objects. So perhaps its not something a company or an organization can just manufacture and provide, perhaps its not something you can just buy off of a store shelf or even win from an extensive contest.

No, I think this particular Starter Kit is more of a mindset than anything else. Its a mindset and a set of things and relationships that an Entrepreneur must acquire to get started in Entrepreneurship. You may not be able to acquire it all at once, and I’m by no means saying that you shouldn’t “start” until you get these things — but I think it is a thing to have as a “checklist” of sorts.

So without further adieu…

The Entrepreneur’s Starter Kit

1. Three years: I’ve said this before in my previous posts, but I thought it’d be prudent to start here. When you’re embarking on Entrepreneurship, give yourself three years. Thats how long it will take for you to become an overnight success (if you’re one of the lucky few).  And that is certainly how long it’ll take for you to bumble around, try enough things, and figure out what actually works.
2. A Constant: Everyone says this, but you have no idea how true this actually is. You will experience the highest of highs and the lowest of lows. So, as you’re embarking on this journey, make sure you have something or someone to hold on to. Something or someone that you can always go back to to compare how far you’ve come over this three-year journey that you’ve embarked on. Something or someone that will help you truly gauge whether you’ve made incremental success and something or someone that will help you gauge when you’ve just messed up. Something or someone that will help you truly gauge your progress, because the last thing you want to do is benchmark your progress compared to the overnight successful startup that TechCrunch is writing about (hint: because Techcrunch didn’t write a line about them during the first 2.5 years they were hustling it).
3. Skills: This may sound obvious, but if you’re going to be doing a tech startup, you better get yourself or someone on your team with tech skills, with business skills and with design skills. No one is telling you that these skills have to be excellent and world class, and no one is telling you that these have to be composed of 3 people (i.e. they can all be you), but make sure you account for these skills — otherwise, don’t bother.
4. Domain Knowledge: If you’re building a startup for the wedding industry, get yourself married or get someone as an advisor  or on your team that has gotten married. If you’re building a fitness startup, make sure you’re not fat. — its as simple as that. With whatever idea you are bumbling around with, make sure you’re doing it with Domain Knowledge. Even if you can’t find an advisor or team member with domain knowledge, do what Hollywood actors do — “get into the role.”
5. Money: Suppose you agree with #1 that it’ll take you about three years of bumbling to get to success. If you’ve had prior exits then it’ll be relatively easy for your to get 3 years of runway right off the bat (or so I’ve heard). If you’re brand new, don’t bother, you’re not getting it. So figure out a way to get yourself chunks of time. Now, obviously, seeking funding is not the only way, which is why I call this section Money. Friends, Family, money stashed away from your previous day job are all sources of money. Figure out what works well for you and make sure you can live and have your mind in a state where you can focus on the goal at hand: to build a business.
6. Someone that often asks you “Are you having fun?”  – One of my investors routinely does this. He’s been through this a number of times before, and whenever I see him, he’s not looking for the PR-version of how things are going. He knows how its going. He just wants to know, “Are you having fun?” — If not, then none of this is worth it.
7. Someone that often asks you “Have you tried X?” - I’ve been fortunate enough to have more than a few investors/advisors that constantly brainstorm with me on how we can make the business better and get closer to achieve our goal. Truth is, most of the suggestions are things you’ll have already thought of, but it serves as a fantastic prioritization process for what to do next. The obvious ideas that keep cropping up in discussions are often the ones to move on. You’ll have a million possible things you can be doing — picking the right one is important — so make sure you set yourself up for having lots of discussions around this.
8. Someone that tells you when its time to move on or try something new - I said three years, but I never said three years on the same idea. The key to Entrepreneurship (I think) is to keep an open mind about what you’re working on and how. Being open and trying new things is critical and its important that you always have an outside factor to remind you. For this, I always count on my friends not in the tech industry, Doctors, Lawyers, Account Execs whom I like to hang out with on a regular basis to give me the right perspective and fresh ideas on things we can all work on to make the world better.
9. Someone that pulls you away from work – I tried the whole work 100+ hours a week. It is a terrible model and it does not scale. Make sure you have someone that pulls you to still stop and smell the flowers. Otherwise, you’ll never survive your three years.
10. A family – You can’t build a business yourself. You want to build a family around you. This checklist item will probably never get checked off — its an asymptotic thing that you’ll constantly strive for, but it is an important to strive for. Make sure you have people to celebrate with in the end once you’ve won.

In Conclusion

I don’t think this list is exhaustive, but I guess its not meant to be. In my limited experience, I think these are the things you need as an Entrepreneur to get started. That and a whole lot of perseverance. Keep it real and make sure you enjoy your three years. Its only the beginning.

What a difference a year makes. It feels just like yesterday I finished up that informal meeting. Its one of my most vivid memories from the past year. We finished talking, I helped hail a cab for Bryce, and then rushed to grab a cab for myself so I could trek uptown to a special dinner date my wife had planned for my Birthday.

It turned out to be a surprise birthday party with some of my closest friends…. what an amazing night it turned out to be.

Fast forward one year to today. Once again, it was my birthday, and as with birthdays go, you can’t help but pause and reflect on what has changed over your lifetime and most importantly, what has changed in just one year. 365 days later, countless investment pitches later, after raising a round, building a team, growing a product, losing a team, rebuilding a team, and keeping on keeping on, here are my reflections from 2011.

Looking back on 2011

These days, I have a tough time remembering the actual year we’re in. It still feels like last year was 2009, except its 2012, and 2011 was probably one of the most transformative years in my life — even though when I reflected on 2010, I said the same thing.

In 2011, I stopped doing a whole bunch of things:

• Stopped working on Braintrust,  the group collaboration tool that was supposed to kill email.
• Stopped working on Main Street, the instant web site builder for small businesses.
• Stopped my consulting business and all projects that came long with it.
• Stopped doing my weekly podcast.

• Doubled down on Tout and decided to put all my heart, soul and sweat into making it a real business.
• Wrote a blog entry about how Tout came to be and won a whole bunch of stuff.
• Joined the 500 Family.
• Raised $350k from Esther Dyson, Dave McClure, Eric Ries, Venture51 and some more seriously awesome angels most of whom have proved to be seriously awesome mentors.
• Built a team around Tout, lost the whole team, and then started to rebuild the team once again.

In 2011, I also truly learned what it means to be completely consumed by ONE thing:
I kissed my wife goodbye, said goodbye to my friends and moved from New York to Mountain View for the summer accelerator program. I was even able to convince a friend to move for the summer and join Tout. It was an amazing and intense few months and it followed a few months of being completely burnt out which made me question whether it was worth it in the end.

Ah and also, In 2011, my wife and I made the decision to pack up our lives and move to San Francisco. Therefore, I  moved Tout and the entire business to San Francisco as well. And with that, I moved to rebuild the entire Tout team in San Francisco as well.

And finally, in 2011, I took something that started off as a simple weekend project to solve my own problem and turned it into a real product that thousands of people use to run and grow their businesses in amazing ways.

Lessons Learned from 2011

2011 was an intense year of growth, learning, joy, thrill, FUN, and pain.

Everything they say about Entrepreneurship is true. It takes you through the highest of highs, the lowest of lows, and tests your courage and challenges you at every single moment. If you’re going to do this, think twice, and then grab on to something that can ground you — because it is going to be an intense ride.

If you aren’t having days where you start off with “What am I doing with my life?!” peak the day with “Holy shit, we’re going to be a billion dollar company” and go to bed with “God, there’s so much to do, please help me” — then you’re probably doing it wrong.

With that said, I think the single biggest lesson learned from 2011 for me is to learn to be more self-aware: As you take on bigger challenges, and bigger goals, and grow your team, it always becomes inevitable that your own voice, your own gut, and your own instincts start to get drowned out compared to all the other (sometimes more experienced) voices. Don’t let it. The biggest mistakes I made in 2011 stemmed from my failure to stop and hear my own voice. If you feel pain, figure out why. If you feel overwhelmed, hit the Pause button (force it).

Figuring out the perfect balance between being open minded, self-reflective, and confident is the secret to being a great Entrepreneur. And its one balance that I plan on continuing to perfect in 2012.

Looking Forward to 2012

It takes 3 years for a startup to become an overnight success. Each year brings its own set of challenges but the goal stays the same. So unlike previous years when I had a full on game plan on how the coming year would be different, this time around, its really more of the same.

I plan to continue to focus on two key things in 2012:

• First and foremost, continue to grow ToutApp into a truly awesome business, and,
• secondly, continue to contribute and advance the art of Entrepreneurship by sharing my learnings.

In Conclusion